Airlines with flights from San Juan to Chicago
There are three airlines with scheduled flights between SJU and MDW. Southwest is the only airline with non-stop flights from Luis Munoz Marin International to Midway International Airport and the flight time is 5 hours.
There are three airlines with scheduled flights between SJU and MDW. Southwest is the only airline with non-stop flights from Luis Munoz Marin International to Midway International Airport and the flight time is 5 hours. Choose airline
Direct
Non-stop
5h 0min
Via Orlando
6h 20min
Via Tampa
6h 25min
Via Atlanta
6h 41min
Via Fort Lauderdale
6h 50min
Via Baltimore
6h 55min
Via Nashville
6h 55min
Via Orlando
7h 58min
Via Saint Louis
7h 20min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 5 hours
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
2 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SJU
Direct
MDW
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN2177
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----
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----
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05:30
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WN3639
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----
----
----
----
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16:30
The timetable & schedule information was updated at 2026-04-21
Via Orlando with Southwest Airlines
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Total flight time: 6h 20m - 13h 15m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
185 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SJU
Via MCO
MDW
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN3721
WN4037
WN4037
05:00
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----
05:00
05:00
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05:00
WN3721
WN2653
WN2653
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05:30
05:30
----
----
----
----
WN3721
WN1418
WN1418
----
----
----
----
----
06:00
----
WN3722
WN1456
WN1456
----
----
----
----
----
----
06:25
WN3722
WN2657
WN2657
06:30
----
----
06:30
06:30
07:00
----
WN3722
WN2653
WN2653
----
07:00
07:00
----
----
----
----
WN3723
WN2657
WN2657
----
----
----
----
----
09:10
----
WN3723
WN2717
WN2717
09:50
----
----
09:50
09:50
----
----
WN3723
WN3874
WN3874
----
09:50
09:50
----
----
----
----
WN3723
WN1734
WN1734
----
----
----
----
----
----
09:50
WN2592
WN2617
WN2617
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----
----
----
----
----
11:35
WN2592
WN2658
WN2658
11:35
----
----
11:35
11:35
----
----
WN3726
WN2659
WN2659
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12:20
12:20
----
----
----
----
WN3724
WN1929
WN1929
----
----
----
----
----
12:25
----
WN4959
WN2659
WN2659
13:15
----
----
13:15
13:15
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----
WN4959
WN2660
WN2660
----
13:30
13:30
----
----
----
14:00
WN3491
WN2660
WN2660
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----
----
----
----
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15:05
WN3726
WN4762
WN4762
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16:20
WN3491
WN4762
WN4762
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----
----
----
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16:40
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WN4613
WN4762
WN4762
18:30
----
----
18:30
18:30
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17:40
The timetable & schedule information was updated at 2026-04-21
Via Tampa with Southwest Airlines
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Total flight time: 6h 25m - 12h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
27 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SJU
Via TPA
MDW
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
WN3730
WN4033
WN4033
07:00
06:00
06:00
07:00
07:00
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----
WN3730
WN1655
WN1655
----
----
----
----
----
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06:05
WN3731
WN4031
WN4031
----
----
----
21:55
21:55
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 6h 41m - 10h 40m.
-
Sky Team Alliance
-
85 flights per week
SJU
Via ATL
MDW
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
DL1879
DL2417
DL2417
06:00
06:00
06:00
06:00
06:00
06:00
06:00
DL1763
DL1728
DL1728
07:30
07:30
07:30
07:30
07:30
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07:30
DL1763
DL2417
DL2417
----
----
----
----
----
07:30
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DL1757
DL1076
DL1076
12:56
12:56
12:56
12:56
12:56
12:56
12:56
DL1882
DL1076
DL1076
14:42
14:42
14:42
14:42
14:42
14:42
14:42
The timetable & schedule information was updated at 2026-04-21
Via Fort Lauderdale with Southwest Airlines
-
Total flight time: 6h 50m - 9h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
16 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2
SJU
Via FLL
MDW
W31, Jul 27 - Aug 02
Flight
Mon
Jul 27
Tue
Jul 28
Wed
Jul 29
Thu
Jul 30
Fri
Jul 31
Sat
Aug 1
Sun
Aug 2
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
Via Orlando with Frontier